Hey Reader! 👋

What happens when the "logical" path leads to a dead end?

In this week's episode of The Story I'm Telling Myself Podcast with Rita Ernst we uncovered these valuable nuggets you need to hear.

.Insight 1: Choose the Life, Not the Job

One of the most striking "gems" from the conversation was guest Ann Njoroge’s shift from seeking a successful career to seeking a successful life. She argued that most people choose a job and then try to fit their life around it, but she reversed the framework. Ann realized she wanted location freedom—specifically the ability to live in a coastal town and work remotely. As Rita summarized, "The goal is the life. The goal is not to be a successful social media or podcast promoter... The goal is about living the life that you want". When your vision is bigger than just making money, it provides the "capacity to live that life" and the tenacity to endure rough patches.

Insight 2: The Reality of the "Runway"

Ann was refreshingly honest about the setbacks. Her first attempt at entrepreneurship didn't yield immediate profit, forcing her to move back home for a year and a half—a period she described as "rock bottom," when she felt she was "being left behind" by her peers. Rita pointed out that many entrepreneurs fail because "they don't give themselves a long enough runway". Success rarely happens in three or six months; it requires a long-term mental and financial commitment to stabilize. Ann eventually returned to traditional employment for three years to regroup before launching again with a more resilient mindset.

Insight 3: Safety vs. Power

Perhaps the most provocative point of the episode was the discussion on "Plan B." For her final, successful leap, Ann decided to have only a "Plan A". She anchored herself in the promise that she would not run back to employment when times got hard. This was supported by a powerful quote from author Peter Block: "When you choose safety and security, you give up your power". By clinging to a safety net, you inadvertently bleed away the commitment and agency needed to make your primary dream work.

Reader, here are three steps to integrate this wisdom right now

1. Conduct a "5-Year Lifestyle Audit": Stop looking at job titles and instead define exactly how you want your Tuesday morning to look five years from now. Ask yourself: "Is what I'm doing now going to make me happy with this decision in five years?"
2. Redefine Your "Runway": If you are currently in a transition or starting a business, stop judging your progress on a 3-month timeline or by comparing yourself to others. Acknowledge that real stability often takes years, not months, and adjust your expectations to prevent burnout.
3. Identify Your "Power Leak": Pinpoint where your "Plan B" or safety net is actually preventing you from going all-in. Determine one area where you can stop playing it safe and start betting fully on your own potential.

​You can catch the whole conversation here​

The journal has a new name: TSITM Episode Activation Guide. Here's your copy: TSITM ep 64 activation guide.pdf​

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Enjoy & share this with a friend!

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